Turning 40 — Is It Ever Too Late to Startup?…

Six months before I turned 40, I took the biggest risk of my career by leaving the world of large institutions and heading to a place where the only thing certain is uncertainty.

I decided I wanted to get over my fear of failure before this big birthday.

For previous generations, a mid-life crisis meant you bought an expensive car, had an affair with someone not age-appropriate, or took off on a trip somewhere exotic. My generation seems to be having more of a mid-career crisis. Instead of buying a convertible, we are starting our own businesses, deciding to consult or freelance or, like in my case, joining a startup.

Why do something so radical? Well…what have we got to lose? Who knows if we will even have social security payments by the time we are of age? Even if we carefully curate our 401Ks will they ever be worth anything in 20 years? Will the long-term job and the retirement home in Florida be a reality? And do we even want it to be?

With the world often in chaos around us, many of my friends are taking a less traditional approach. Instead of pursuing money and security, we are pursuing happiness and quality time.

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When I ask people my age what’s most important to them, it’s flex-time and creative freedom. No one wants to be locked to a desk and a daily routine. Things are changing rapidly. We may be witnessing the end of “office life” altogether as more and more work happens through technology. I see both the good and the bad in that. I still remember a world without email — you had to call someone on the phone to work things out. (I still rely on this ancient tactic occasionally. I’m old-school.)

One of the best parts of my new job are the days I get to work remotely. We are an online company, and most of my work happens on my phone or laptop. It doesn’t mean I work any less, sometimes I work even more. But I can do it from anywhere and that’s a game-changer. It means two hours of every week of my life back without spending it on a train into the city. I get to drop my kids off at school every morning and kiss them goodbye, which is worth more to me right now than any normal 9-5 job could ever offer me.

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Tomorrow is never promised to us, it’s an assumption. While I am not recommending all Gen-Xers abandon your current jobs and start screaming “YOLO,” I will tell you to trust yourself. When it was time for me to consider a world of entrepreneurship, I knew I was willing to place a bet on myself. Age isn’t just a number, it’s a mark of experience. I would bet far more on the person I am today than the young woman I was in my 20s.

I gave the following advice to someone considering a career-shift like I’ve made:

“If you are going to jump out of that plane, you need to do it now. When we were younger, we didn’t know what we were doing. We’ve been working for 20 years now. We know this world inside and out. We understand the rules but we still have time to re-invent the game. We got this.”

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I’m proud of who I’ve become. I’m owning my age. I have tried to gracefully go gray (and then decided against it, I’m not perfect). I have begun to understand I will always look a certain way and have faults that are a part of who I am and do not count against me. The older I have gotten the more I accept myself. I know who I am and I’m ready for what’s next.

Older and wiser and more prepared than ever, I continue to navigate this new world of a startup. I have experienced every emotion available. I have worked until my brain hurt almost every day. The best part is, even as I age, I have never felt more alive. You are never too old to follow your heart or your gut. Don’t forget that. Now excuse me as I have to save my breath to blow-out all the candles on my cake.

Victoria Cairl

Victoria Cairl writes about women and work. She’s is the VP of Business Development at Show-Score, a lover of Broadway and mother of three.  

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